Guest Stars Jon Huertas as Miguel Rivas Lonnie Chavis as Young Randall Pearson Janet Montgomery as Olivia Maine Da'Vine Joy Randolph as Tanya Ric Sarabia as Pilgrim Rick Kate Blumberg as Kate's Flight Seat Mate Co Starring Eris Baker as Tess Pearson Faithe Herman as Annie Pearson Parker Bates as Young Kevin Pearson Mackenzie Hancsicsak as Young Kate Pearson Caitlin Thompson as Madison Jill Lynne Johnson as Laurie Julia Cho as Jill Chris Grace as Paul Danielle Pinnock as Ruth Dan Considine as Gas Station Employee Carlin James as Male Flight Attendant